Isopropyl iodide → HCID 53241572, compound

HRID 1454048Notes

Reaction equation

HRID 1454048 reaction equation
[CH2:1]1[CH2:11]CN2C(=NCCC2)C[CH2:2]1.[OH:12][CH:13]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:29](=[O:30])[CH2:28][CH2:27][C@@H:26]2[CH2:31][CH2:32][CH2:33][C:34]2[S:38][C:37]([C:39]([OH:41])=[O:40])=[CH:36][CH:35]=2)=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].IC(C)C>CC(C)=O>[CH:1]([O:40][C:39]([C:37]1[S:38][C:34]([CH2:33][CH2:32][CH2:31][C@H:26]2[CH2:27][CH2:28][C:29](=[O:30])[N:25]2[C:22]2[CH:21]=[CH:20][C:19]([CH:13]([OH:12])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:24][CH:23]=2)=[CH:35][CH:36]=1)=[O:41])([CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11855868HCID 11855868, compound

Product 1

HCID 53241572HCID 53241572, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

DBU (5.2 μL, 0.035 mmol) was added to a solution of acid 43 (7.5 mg, 0.017 mmol) in acetone (0.1 mL) at rt under nitrogen. After 10 min, 2-iodopropane (35 μL, 0.35 mmol) was added. After 21 h at rt, the reaction was quenched with 0.01 N HCl (3 mL) and extracted with EtOAc (3×4 mL). The combined extracts were washed with brine (5 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica (CH2Cl2→1% MeOH CH2Cl2) afforded 4.6 mg (53%) of the title compound (44).

Workup

  1. waitAfter 21 h at rt
  2. customthe reaction was quenched with 0.01 N HCl (3 mL)
  3. extractionextracted with EtOAc (3×4 mL)
  4. washThe combined extracts were washed with brine (5 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography on silica (CH2Cl2→1% MeOH CH2Cl2)

Sources & evidence

ORD record
ord-38131bf06da24263b8ba2c62433c0995
Source dataset
uspto-grants-2009_01
Patent number
US07476747B2

Reaction notes

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